Sodium Carbonate → HCID 59374240, compound

HRID 473674Notes

Reaction equation

HRID 473674 reaction equation
Cl[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[O:23]1[CH2:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[O:23]1[CH2:24][CH:25]=[C:26]([C:2]2[C:3]([O:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]4[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=4)=[CH:11][CH:10]=3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 59374316HCID 59374316, compound

Product 1

HCID 59374240HCID 59374240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a glass microwave vial was added N-(4-(3-chloropyrazin-2-yloxy)phenyl)-3-fluoropyridin-2-amine (0.2824 g, 0.892 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.281 g, 1.337 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (0.050 g, 0.071 mmol), and sodium carbonate (0.473 g, 4.46 mmol) in DME (2.378 mL) and Water (0.594 mL). The reaction mixture was stirred and heated in a Discover® model microwave reactor (CEM, Matthews, N.C.) at 100° C. for 20 min (60 watts, Powermax feature on, ramp time 5 min). The crude product was adsorbed onto a plug of silica gel and chromatographed to provide N-(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)phenyl)-3-fluoropyridin-2-amine. MS (ESI, pos. ion) m/z: 365.0 (M+1). IC50 (uM) 0.0.0217.

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-c92fc43b7a5f4ad998d0722511d0674c
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

Loading…